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His American Dream

Bloomberg informs me that barely a day goes by without someone urging him to run. So? “If you ask me in my heart of hearts,” he says, “I don’t think that my view will change that I have a better job, I’d like to finish out what I’m doing here and then try something brand-new, which is challenging, in philanthropy ... I was elected for four years. Now, everybody says this is ridiculous, but I take it seriously—though I don’t know that it’s a be-all and end-all thing ... Then there’s practical aspects of, ‘Hey, pro-choice, pro–gay rights, pro–science and evolution, against guns’—I don’t know that I’d ever have the opportunity. My mother keeps saying, ‘Don’t let it go to your head,’ but I’m sure she likes the articles.”

Bloomberg’s answer is reasoned, measured, and blessedly wink-free—but it’s also riddled with elisions and escape clauses wide enough to drive a Hummer through. For one thing, Bloomberg’s socially liberal positions would only be a problem if he were seeking the Republican nomination, an eventuality roughly as plausible as his becoming pope. And a Democratic candidacy is almost as unlikely. No, if Bloomberg were to enter the fray, it would be as an independent.

Whether that happens will likely depend on two factors: who the two parties pick as their standard-bearers and the mood of the country. Bush’s longtime media guru, Mark McKinnon, who now advises McCain, contends that “if a year from now there hasn’t been much progress or bipartisanship, and if the primaries do what they often do and squeeze out the moderates, you’ll have an ideal situation for a third-party run.” Sheekey, in fact, has publicly laid out the most likely Bloomberg-friendly scenario: McCain is beaten by someone to his right (Mitt Romney, say) and the Democrats choose someone generally seen as unelectable (guess who?).

By itself, however, even the presence of the Arizona senator in the race might not deter the mayor. “McCain, is he a viable candidate?” Bloomberg muses. “Is it McCain from the ‘Straight-Talk Express’ or the guy that went to Liberty University?” For emphasis, he adds, “He is a very nice guy ... but I also think he’s pretty conservative.”

Bloomberg being Bloomberg, his ultimate decision will be well considered and ruthlessly pragmatic. “When he ran for mayor, he had to have a clear path in his mind about how he could win,” says Cunningham. “There would have to be a combination of factors where he believes there’s a road map that gets him to 1600”—1600 Pennsylvania Avenue, that is.

All of which is why some Bloomberg confidants believe the odds are low that the mayor will bring himself to pull the trigger. “He views running as an independent as a triple bank shot,” says a friend. “He hasn’t closed his mind to it, but the probabilities are he won’t get comfortable with that.”

But Sheekey remains hopeful. “I think he’s giving you an honest answer [in saying he does not intend to run]. That said, he’s looking at a moment in time, and things may be different in a year—more and not less partisan rancor and gridlock, less and not more attention to long-term issues, a much greater desire in the country for an independent candidacy. The question is whether he would change his mind. And I do think it’s a possibility.”

David Garth—the storied New York political consultant who helped Giuliani and Bloomberg—holds a more definite view. “There’s been a subtle change in Mike in the past couple of years,” Garth says. “In the beginning, I don’t think he saw himself as a potential candidate for president. But as time went on, he started to become more of a believer, mainly in his potential.” Garth pauses. “Mike is not the kind of person who says, ‘I’ll just throw my hat in the ring’; neither is Rudy, for that matter. But my feeling is, they’re both going to be there at the end.”

If Bloomberg is there at the end, his chances will depend much on Sheekey. “I can’t think of anyone better-qualified to run a national campaign,” says pollster Doug Schoen, whose clients have included Mr. and Mrs. Clinton as well as Bloomberg. “He’s big-time,” concurs Mark McKinnon. “He’s got the James Carville–Karl Rove DNA.”

Sheekey’s game plan for 2008 begins with the premise that the mayor can afford to wait until early that year to jump. And afford is the proper term, for mounting a tenable independent campaign would likely cost $250 million to $500 million. For most fantasy-league candidates, raising that kind of dough would take years, if not decades. For Bloomberg, it would take, figuratively speaking, a trip to the ATM. (“Half a billion dollars?” he said to someone at a party this year. “Not a problem.”)